When my wife and I separated, I found myself living for a while at a hotel. Nothing fancy, just a Days Inn.
I had often fantasized about what it would be like to be with another guy, maybe jerking off together, maybe more. The ex and I had engaged in anal play every so often and I had begun to like it when she fingered my ass.

During this time I was also smoking a lot of weed and drinking a lot. One night when I was plenty stoned and a little horny I decided to post an ad on Craigslist. Wasn't really expecting anything to come of it. MAYBE someone would send me a pic. MAYBE I would jerk off by myself and fall asleep. However, I got a response from someone in town on business but at a different hotel. I told him that I had never been with a guy before but that I was interested in playing with another cock, maybe working up the nerve to suck it - maybe, just maybe - getting fucked. He had been with other guys before and he was accepting of my inexperience.

For whatever reason - I told him to come over, bring a few beers, some condoms and lube and we'd see what happened.

He showed up a half hour later.

I was very nervous but he was easy to talk to. He stood about 2 inches taller than me and had a build like he worked out sometimes. We laid back on the bed, started drinking a beer, engaged in a little small talk.

After what seemed like 5 minutes he looked at me and asked if we should get more comfortable.

I said, "Ok".

We stood up. We faced each other and I began taking his shirt off. Then, for the very first time, I kissed another man. It was exciting and thrilling and it was very passionate. I began to rub on his torso and kiss on his chest as he started undressing me. When I pulled his pants down I got the nerve to reach down and grabbed his bulge. I had never touched another cock before and here was one getting harder by the second.

He went to the edge of the bed and laid down. I kissed on his nipples, running my hands over his body, fascinated by it.
I reached his underwear, pulled them down and noticed he had a thick cock with a huge mushroom head. I began thinking that there was no way I would fit this in my mouth. I started fondling it, kissing his balls, stroking his cock as I felt it get even harder in my hand. It didn't take me long to work up the nerve to lick it, eventually opening my mouth wide to get my first taste of cock.

I'm sure he could tell that I didn't quite know what I was doing but he let me go on for a few minutes. He then stopped me, sat up and kissed me and told me to lay down.

I was naked and hard and he knelt between my legs and began sucking me off. I watched him, fascinated at the sight of another guy sucking my cock.

He sucked it for a few minutes before I looked at him and told him that I wanted him to fuck me.
He went over, grabbed the condoms and lube and got his cock ready for me.

I opened my legs and held them open wide, like my ex had always done for me. I was nervous but ready.
He got between my thighs and I watched him slide his cock up and down my asshole. I told him, again, to fuck me. He started sliding it gently inside me. I could feel my ass tightening up and had to remind myself to let those muscles relax. He could feel me starting to give in and he pushed his cock in a little deeper. He put his body on top of mine, I wrapped my arms around him and he began to fuck me faster and deeper.

I was surprised at how good it felt, even though it was hurting a little too. I loved feeling it slide in and out of my ass. He raised his body and I grabbed my ankles, all the while talking dirty to him. Telling him to fuck my tight ass. how much I loved his hard cock inside me.

He reached down and started stroking my cock while he fucked me. It didn't take long before I came all over my chest and stomach. He got up, grabbed a towel and cleaned me off.
Still hard, he told me to turn over and I got on my stomach, my legs spread. He climbed on top and began to fuck me hard and fast. I could tell he wanted to cum so I started talking to him as dirty as I knew how. Before long, he pulled out, ripped the condom off and shot a huge load all over my back.

I laid there, ass gaping, covered in cum, wishing I had told him to cum in my mouth.

He cleaned me off again, got himself together to leave as I stayed in bed basking in the fact that I just had another man inside of me.

I never saw him after that, but I still think of that experience from time to time. It never fails to get me hard.